US2572867A - Rodenticide comprising fluoroacetphenylhydrazide - Google Patents
Rodenticide comprising fluoroacetphenylhydrazide Download PDFInfo
- Publication number
- US2572867A US2572867A US78454A US7845449A US2572867A US 2572867 A US2572867 A US 2572867A US 78454 A US78454 A US 78454A US 7845449 A US7845449 A US 7845449A US 2572867 A US2572867 A US 2572867A
- Authority
- US
- United States
- Prior art keywords
- rodenticide
- fluoroacetphenylhydrazide
- water
- vol
- proven
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003128 rodenticide Substances 0.000 title description 13
- SNFXTZXIXWPTLF-UHFFFAOYSA-N 2-fluoro-n'-phenylacetohydrazide Chemical compound FCC(=O)NNC1=CC=CC=C1 SNFXTZXIXWPTLF-UHFFFAOYSA-N 0.000 title description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 241000209149 Zea Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- RJBYSQHLLIHSLT-UHFFFAOYSA-N methyl 2-fluoroacetate Chemical compound COC(=O)CF RJBYSQHLLIHSLT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
Definitions
- the present invention has provided a new rodenticide in the form of fiuoroacetphenylhydrazide which has proven to be practically insoluble in water and of greatly improved efiiciency.
- Fluoroacetphenylhydrazide may be expressed by the following formula:
- Example 1 This compound may prefer-ably be obtained in its laboratory form in the following manner:
- Example 2 When prepared commercially in its relatively impure form fluoroacetphenylhydrazide has a pronounced tan color. It is obtained by crystallization as described in Example 1, with parts of fluoroacetate heated with 12 parts of phenylhydrazine. It is preferred, when using fluoroacetphenylhydrazide as a commercial rodenticide, to add a coloring matter to the rodenticide so that the color will act as a warning against accidental use of the rodenticide for other purposes. Such coloring matter may be in the form of any suitable insoluble dye, such as du Pont Oil Blue, a dye well known in the art, added in an amount to give the concentration of color desired.
- a coloring matter may be in the form of any suitable insoluble dye, such as du Pont Oil Blue, a dye well known in the art, added in an amount to give the concentration of color desired.
- fluoroacetphenylhydrazide is unusually stable. It remains stable after storage at C., after irradiation by filtered ultra-violet light, and after heating to fusion.
- the insolubility of the rodenticide of the present invention affords many hitherto unobtainable advantages over prior rodenticides which have varied degrees of solubility in water. Most important of all, the rodenticide of the present invention is not affected or leached out by water, moisture or outside exposure to extreme weather conditions. It tends to remain where placed, but if it should be carried away by currents of water, as in a barnyard, it would not contaminate sources of drinking water, and it would merely settle to the bottom of a container of water. When coloring matter is used, the fluoroacetphenylhydrazide would become apparent in any appreciable concentrations that might have collected in drinking water.
- a rodenticide comprising a mixture of corn meal and fiuoroacetphenylhydrazide that contains approximately 1% of fluoroacetphenylhydrazide.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Oct. 30, 1951 OFFICE RODENTICIDE COIVIPRISING FLUOROACET- PHENYLHYDRAZIDE Leonard Karel, Silver Spring, and Benjamin Witten, Baltimore, Md.
No Drawing. Application February 25, 1949, Serial No. 78,454
1 Claim (01. 167-46) (Granted under the act of March 3, 1883, as amended April 30, 1928; 370 0. G. 757) This invention relates to rodenticides, and more particularly to a novel rodenticide that is substantially insoluble in water.
Prior rodenticides, such as fluoroacetate, known in industry as 1080, have had the disadvantage that they were critically soluble in water, which seriously restricts their use and effectiveness.
The present invention has provided a new rodenticide in the form of fiuoroacetphenylhydrazide which has proven to be practically insoluble in water and of greatly improved efiiciency. Fluoroacetphenylhydrazide may be expressed by the following formula:
CHZF
only
Example 1 This compound may prefer-ably be obtained in its laboratory form in the following manner:
Add 1 ml. methyl fluoroacetate (1.17 g., 0.0127 mole) to 1.2 ml. phenylhydrazine (1.3 g., 0.0122 mole). Heat in boiling water for two hours. Cool in ice to crystallize. Collect the crystals on a filter and Wash with 1-2 ml. cold benzene. Yield is near quantitative. These crystals have a melting point of 103.6 to 105 C.
Example 2 When prepared commercially in its relatively impure form fluoroacetphenylhydrazide has a pronounced tan color. It is obtained by crystallization as described in Example 1, with parts of fluoroacetate heated with 12 parts of phenylhydrazine. It is preferred, when using fluoroacetphenylhydrazide as a commercial rodenticide, to add a coloring matter to the rodenticide so that the color will act as a warning against accidental use of the rodenticide for other purposes. Such coloring matter may be in the form of any suitable insoluble dye, such as du Pont Oil Blue, a dye well known in the art, added in an amount to give the concentration of color desired.
Tests have proven that when fiuoroacetphenylhydrazide is used in doses as small as 10 grams of fluoroacetphenylhydrazide per kilo. of edible matter it has proven lethal to large percentages of the various animals tested. DOSes of from 1-2% of fluoroacetphenylhydrazide mixed with corn meal produced a 100% lethality in rats.
Toxicity and acceptability tests on other types of rodents have also proven extremely effective. Furthermore, fluoroacetphenylhydrazide is unusually stable. It remains stable after storage at C., after irradiation by filtered ultra-violet light, and after heating to fusion.
The insolubility of the rodenticide of the present invention affords many hitherto unobtainable advantages over prior rodenticides which have varied degrees of solubility in water. Most important of all, the rodenticide of the present invention is not affected or leached out by water, moisture or outside exposure to extreme weather conditions. It tends to remain where placed, but if it should be carried away by currents of water, as in a barnyard, it would not contaminate sources of drinking water, and it would merely settle to the bottom of a container of water. When coloring matter is used, the fluoroacetphenylhydrazide would become apparent in any appreciable concentrations that might have collected in drinking water.
The present invention is not limited to the preferred examples herein described, but includes all of its embodiments and modifications within the spirit and scope of the appended claim.
We claim:
A rodenticide comprising a mixture of corn meal and fiuoroacetphenylhydrazide that contains approximately 1% of fluoroacetphenylhydrazide.
LEONARD KAREL. BENJAMIN WITTEN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,177,598 Herzig et a1 Oct. 24, 1939 2,390,848 Richter Dec. 11, 1945 OTHER REFERENCES Gatterman et al.: Berichte der Deutsche Chemische Gesellschaft, vol. 25, pp. 1080. (Copy in Pat. 01f. Lib.)
McCombie et al.: Nature, September 14, 1946, vol. 158, pp. 382-385.
Science, vol. 102, No. 2644, pp. 232, 233, August 31, 1945.
Slegler et al.: J. Econ. Ent., vol. 39, No. 3, p. 416, June 1946.
Karel: J. Pharmacol. and Exptl. Therap., v01. 63, No. 3, pp. 287-293, July 1948.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78454A US2572867A (en) | 1949-02-25 | 1949-02-25 | Rodenticide comprising fluoroacetphenylhydrazide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78454A US2572867A (en) | 1949-02-25 | 1949-02-25 | Rodenticide comprising fluoroacetphenylhydrazide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2572867A true US2572867A (en) | 1951-10-30 |
Family
ID=22144129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US78454A Expired - Lifetime US2572867A (en) | 1949-02-25 | 1949-02-25 | Rodenticide comprising fluoroacetphenylhydrazide |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2572867A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092660A (en) * | 1957-07-03 | 1963-06-04 | Hoffmann La Roche | 1-acyl-2-alkyl-hydrazine derivatives |
| US5367093A (en) * | 1991-11-22 | 1994-11-22 | Uniroyal Chemical Company, Inc. | Insecticidal phenylhydrazine derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2177598A (en) * | 1936-02-04 | 1939-10-24 | Winthrop Chem Co Inc | Manufacture and application of agents for combating rodents |
| US2390848A (en) * | 1943-12-31 | 1945-12-11 | Nasa | Rodenticide |
-
1949
- 1949-02-25 US US78454A patent/US2572867A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2177598A (en) * | 1936-02-04 | 1939-10-24 | Winthrop Chem Co Inc | Manufacture and application of agents for combating rodents |
| US2390848A (en) * | 1943-12-31 | 1945-12-11 | Nasa | Rodenticide |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3092660A (en) * | 1957-07-03 | 1963-06-04 | Hoffmann La Roche | 1-acyl-2-alkyl-hydrazine derivatives |
| US5367093A (en) * | 1991-11-22 | 1994-11-22 | Uniroyal Chemical Company, Inc. | Insecticidal phenylhydrazine derivatives |
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